Azo dyes and process of making the same.



UNITED. STATES arnum OFFICE-,

ERNST FUSSENEGGER, OF LUDWIGSHAFEN-ON-THE-BHINE, GERMANY, ASSIGNOR TO BADISCHE ANILIN & SODA FATBRIK, F LUDWIGSKKEEN ONJTHE-RHINE, GER.

MANY, A CORPORATION.

AZO DYES AND PROCESS OF MAKING THE SAME.

No Drawing.

subject of the Emperor of Austria-Hungary, residing at Ludwigshafen-on-the Rhine, Germany, have invented new and useful Improvements in Azo Dyes and Processes of Making the Same, of which the following is a specification.

I have found that by combining the diazo I compound obtainable from i-chlor-Q-aminophenol (or a substitution product thereof) with a sulfonic acid of 1.8-acidyl-a1ninonaphthol, coloring matters can be obtained which, upon subsequent treatment with a bichromate, give rise to beautiful violetblue to blue shades of excellent fastness against the action of light, fulling, potting, carbonizing, and sulfur, and which also have good equalizing power.

My new coloring matters are characterized by yielding red to violet-red solutions in water, from red to blue solutions in so-' dium bicarbonate solution and from blue to violet-red solutions in concentrated sulsolution of 405 parts of the disodium salt of 1.8.3.6-acetyl-amino-naphthol-disulfonic acid. Continue stirring at ordinary temperature until the combination complete, and then filter oif the coloring matter (after adding, if necessary, some common salt) and press and dry it.

If desired, the combination can be carried out in acetic acid solution or in alkaline solution, instead of in neutral solution.

In an analogous manner, coloring matters can be obtained by employing a derivative of i-chlor-Qaminophenol, such for instance as a sulfonic acid thereof, and further in Specification of Letters Patent.

Patented Aug. 6, 1912.

Application fileu' April 18, 1912. Serial No. 691,699.

stead of employing 1.8.3.6-acetyl-aminonaphthol-di'sulfonic acid, other sulfonic acid of a 1.8-acidyl-aminonaphthol can be employed.

The following shades are obtainable from some of the dyes made in accordance with my invention Shades obtained by Coloring matter from Direct dye After-treatment ing. with bichromate.

4-chlor-2 -aminophenol 1.8.5- Bordeaux Violet-blue.

acetyl aminonaphthol sul fonic acid. 4-ehlor-2-aminophenol +1.B.3.6- Bordeaux Navy blue.

' acetyl-aminonaplithol (lisultonic acid. 4-chlorfi-amiuophenOl-W'.4. di- Red Violet-blue.

chlorbenzoyl-aminonaphthol- (lisulfonic acid (1.8.4.6). 4-cb.lor2-am.lnophenol-6-sulfon- Bordeaux Navy blue. ic acid 1.8.5 acetylamiuonaphthotsulfonic acid.

Now what I claim is 1. The process of producing azo coloring matters by combining a diazotized i-chlor- 2-aminophenol body with a sulfonic acid of l..8acidyl-amino-naphthol.

2. The process of producing'azo coloring matter by combining 4-chlor-2-diaz0phenol with 1-acetyl-amino-8-naphthol-3.6-disulfonic acid.

The new azo coloring matters which can be obtained by combining a diazotized 4chlor-2-aminophenol body with a sulfonic acid of 1.S-acidyl-aminonaphthol which coloring matters yield red to violet red solutions in water, from red to blue solutions in sodium bicarbonate solution and from blue to violet-red solutions in concentrated sulfuric acid, they dye wool directly from Bordeaux to red shades which on treatmentwith bichromate turn from blue to violet-blue, and on gentle reduction with stannous chlorid give rise to a t-chlorQ- aminophenol body and a mono-acidyl-diaminonaphthol-sulfonic acid;

4. The new azo coloring matter which can be obtained by combining t-chlor-Q- diazophenol with l-acetyl-amino-S-naphthol-3.6-disulfonic acid, which coloring mat ter yields a car-mine red solution in water, a violet solution in sodium bicarbonate solution, a blue solution in concentrated sulfuric acid and dyes W001 directly Bordeaux In testimony whereof I have hereunto set shades, which shades on treatment with bimy hand in the presence of two subscribing chromate turn navy-blue, which coloring Witnesses.

matter on gentle reduction with stannous ERNST FUSSENEGGER. chlorid gives rise to 4-ch10r-2-amin0phen0l \Vibnesses:

and amino-l-acety]amino-8-naphthol-3.6- J05. I-IEIFFER,

disulfonic acid. ERNEST F. EHRHARDT. 

